Undecylprodigiosin

Undecylprodigiosin

File:Undecylprodigiosin.svg
Names
IUPAC name (2Z,5Z)-3-Methoxy-5-pyrrol-2-ylidene-2-[(5-undecyl-1H-pyrrol-2-yl)methylidene]pyrrole
Identifiers
CAS Number	52340-48-4 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29702
ChEMBL	ChEMBL83139 checkY[EMBL]
ChemSpider	10481061 checkY
ECHA InfoCard
E number
PubChem CID	135515151
UNII	ZQ2HK5E6ZG checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C25H35N3O/c1-3-4-5-6-7-8-9-10-11-13-20-15-16-21(27-20)18-24-25(29-2)19-23(28-24)22-14-12-17-26-22/h12,14-19,26-27H,3-11,13H2,1-2H3/b24-18- checkY Key: HIYSWASSDOXZLC-MOHJPFBDSA-N checkY
SMILES CCCCCCCCCCCC1=CC=C(N1)/C=C\2/C(=CC(=N2)C3=CC=CN3)OC
Properties
Chemical formula	C25H35N3O
Molar mass	393.575 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Undecylprodigiosin is an alkaloid produced by some Actinomycetes bacteria. It is a member of the prodiginines group of natural products and has been investigated for potential antimalarial activity.

Natural sources

Undecylprodigiosin is a secondary metabolite found in some Actinomycetes, for example Actinomadura madurae, Streptomyces coelicolor and Streptomyces longisporus.

Production

Biosynthesis

The biosynthesis of undecylprodigiosin starts with PCP apoprotein which is transformed into the holoprotein using acetyl CoA and PPtase then adenylation occurs utilizing L-proline and ATP. The resulting molecule is then oxidized by dehydrogenase enzyme. Elongation by decarboxylative condensation with malonyl CoA is followed by another decarboxylative condensation with L-serine using α-oxamine synthase (OAS) domain. The compound is then cyclized, oxidized with dehydrogenase and methylated with SAM to give 4-methoxy-2,2′-bipyrrole-5-carboxaldehyde (MBC) intermediate which react with 2-undecylpyrrole (2-UP) to give undecylprodigiosin.

File:Biosynth.png

Biosynthesis of undecylprodigiosin

Laboratory

The first total synthesis of the undecylprodigiosin was published in 1966, confirming the chemical structure. As with the biosynthesis, the key intermediate was MBC.

Uses

As with other prodiginines, the compound has been investigated for its pharmaceutical potential as anticancer, immunosuppressant, or antimalarial agent.